MOCA

MOCA is a highly effective aromatic diamine curing agent used in polyurethane elastomers.
MOCA provides excellent mechanical strength, abrasion resistance, and chemical durability.
MOCA's strong reactivity with isocyanates makes it suitable for high-performance industrial applications.

CAS Number: 101-14-4
EC Number: 202-918-9
Molecular Formula: C13H12Cl2N2
Molecular Weight: ~267.15 g/mol

Synonyms: 101-14-4, 4,4'-METHYLENEBIS(2-CHLOROANILINE), MOCA, Bisamine, Cyanaset, 4,4'-Methylene bis(2-chloroaniline), Methylenebis(chloroaniline), Dacpm, Curalin M, Diamet Kh, CL-Mda, Bis amine, Millionate M, Bisamine S, Cuamine M, Cuamine MT, Curene 442, MOCA (curing agent), Bis-amine A, Bis(4-amino-3-chlorophenyl)methane, Rcra waste number U158, Bis(3-chloro-4-aminophenyl)methane, 4,4'-Methylenebis(o-chloroaniline), LD 813, Methylene-bis-orthochloroaniline, 3,3'-Dichloro-4,4'-diaminodiphenylmethane, 4,4'-Diamino-3,3'-dichlorodiphenylmethane, Methylenebis(3-chloro-4-aminobenzene), DTXSID5020865, 4,4-Metilene-bis-o-cloroanilina, 4,4'-Methylene-bis-(2-chloroaniline), Di-(4-amino-3-clorofenil)metano, p,p'-Methylenebis(o-chloroaniline), Benzenamine, 4,4'-methylenebis[2-chloro-, 4-[(4-amino-3-chlorophenyl)methyl]-2-chloroaniline, 4,4'-Methylenebis(2-chlorobenzenamine), Di(4-amino-3-chlorophenyl)methane, Benzenamine, 4,4'-methylenebis(2-chloro-, 4,4'-Methylene(bis)-chloroaniline, Di(-4-amino-3-chlorophenyl)methane, 3L2W5VTT2A, 4,4'-Methylenebis[2-chloroaniline], Methylene 4,4'-bis(o-chloroaniline), 4,4'-Methylenebis-2-chlorobenzenamine, p,p'-Methylenebis(alpha-chloroaniline), p,p'-Methylenebis(ortho-chloroaniline), Aniline, 4,4'-methylenebis(2-chloro-, 2,2'-Dichloro-4,4'-methylenedianiline, 3,3'-Dicloro-4,4'-diaminodifenilmetano, 3,3'-Dichlor-4,4'-diaminodiphenylmethan, 3,3'-Dichloro-4,4'-diaminodifenilmetano, NSC-52954, methylenebis(o-chloroaniline), DTXCID50865, CHEBI:28124, 4,4'-Methylenebis[o-chloroaniline], Aniline, 4,4'-methylenebis[2-chloro-, 4-[(4-amino-3-chloro-phenyl)methyl]-2-chloro-aniline, p,p'-Methylenebis[o-chloroaniline], Methylenebis[3-Chloro-4-aminobenzene], 4,4'-Methylenebis[2-chlorobenzenamine], 4-((4-amino-3-chlorophenyl)methyl)-2-chloroaniline, 4-((4-amino-3-chloro-phenyl)methyl)-2-chloro-aniline, Methylene Bis(chloroaniline), 4,4'-Methylenebis(o-chloro aniline), Benzenamine, 4,4'-methylenebis(2-chloro)-, RefChem:506796, 4,4'-METHYLENE(BIS)CHLOROANILINE, 202-918-9, Quodorole, MBOCA, 4,4'-Methylene-bis(2-chloroaniline), C13H12Cl2N2, MFCD00047829, Methylene-4,4'-bis(o-chloroaniline), 4,4'-methanediylbis(2-chloroaniline), 4,4-methylene-bis(2-chloroaniline), 27342-75-2, p,p'-Methylenebis(.alpha.-chloroaniline), p,p'-Methylenebis[.alpha.-chloroaniline], CCRIS 389, HSDB 2629, 4,4'-Methylenebis(2-chloroaniline) (~90%), EINECS 202-918-9, NSC 52954, RCRA waste no. U158, UNII-3L2W5VTT2A, BRN 1882318, 4,4'-Methylene-bis(2-chloroaniline), analytical standard, 4,4-Metilene-bis-o-cloroanilina [Italian], Di-(4-amino-3-clorofenil)metano [Italian], 4,4'-Diamino-3,3'-dichlorodiphenyl methane, 3,3'-Dichlor-4,4'-diaminodiphenylmethan [German], 3,3'-Dicloro-4,4'-diaminodifenilmetano [Italian], 3,3'-Dichloro-4,4'-diaminodifenilmetano [Italian], CBMicro_013250, 3,4'-diaminodifenilmetano, 3,4'-diaminodiphenylmethan, EC 202-918-9, Cambridge id 5180272, BENZENAMINE,4,4'-METHYLENEBIS[2-CHLORO-, Oprea1_093196, SCHEMBL43509, 1-13-00-00074 (Beilstein Handbook Reference), 78642-65-6, MLS002303002, CHEMBL82846, 4,3'-(dichlorodiphenyl)methane, SCHEMBL30097830, WLN: ZR CG D1R DZ CG, MSK1215, HMS3039N14, 4,4'-Bis(2-chloroanilino)methane, 4,4'-Methylenebis[2-chloroaniline, AAA10114, ALBB-010577, Aniline,4'-methylenebis[2-chloro-, NSC52954, SMSF0004157, Tox21_200651, MSK1215-100M, STK295634, 4,4'-methylene bis(o-chloroaniline), 4,4''-Methylenebis(2-chloroaniline), AKOS000120884, Benzenamine,4'-methylenebis[2-chloro-, CB03526, 2,2'-dichloro-4,4'-methylendianiline, ar,ar'-Methylenebis(2-chlorobenzenamine), NCGC00090906-01, NCGC00090906-02, NCGC00258205-01, CAS-101-14-4, METHYLENEBIS(CHLOROANILINE) [HSDB], SMR001307314, BIM-0013222.P001, Benzenamine, ar,ar'-methylenebis(2-chloro-, DI-(4-AMINO-3-CHLOROPHENYL)METHANE, 4,4'-Methylene-bis(2-chloroaniline), 85%, M0609, NS00005883, ST50319834, EN300-17899, F86374, 4,4'-METHYLENEBIS(2-CHLOROANILINE) [MI], SR-01000197737, [4-(4-Amino-3-chlorobenzyl)-2-chlorophenyl]amine, 4,4'-METHYLENEBIS(2-CHLOROANILINE) [IARC], 4-(4-Amino-3-chlorobenzyl)-2-chlorophenylamine #, Q2257591, SR-01000197737-1, 4-[(4-amino-3-chlorophenyl)methyl]-2-chlorophenylamine, 4,4 inverted exclamation marka-Methylene-bis(2-chloroaniline), 4,4'-Methylene-bis(2-chloroaniline) 10 microg/mL in Acetonitrile, 4,4'-Methylene-bis(2-chloroaniline) Solution in Methanol, 100_g/mL, 4,4'-Diamino-3,3'-dichlorodiphenylmethane;4,4'-Diamino-3,3'-dichlorodiphenylmethane; 2,2'-Dichloro-4,4'-methylene dianiline;DACPM;

MOCA is an aromatic diamine widely used as a curing agent in polyurethane systems.
MOCA is a solid compound at room temperature and is known for providing excellent mechanical strength and chemical resistance in elastomer formulations.
Due to its structure, MOCA reacts efficiently with isocyanates to form highly durable polymer networks.

MOCA is a substance used as a curing agent in polyurethane production.
MOCA is an aromatic amine which is structurally similar to benzidine, a known human bladder carcinogen.

MOCA has been shown to cause hepatomas in mice and rats, lung and mammary carcinomas in rats and bladder cancer in dogs.
MOCA is a proven human carcinogen standing on the WHO List of IARC Group 1 carcinogens, with a current threshold limit value of 0.01 ppm in the industrial atmosphere.
Animal studies have resulted in tumor growth in the liver, lung, and bladder.

MOCA is a weak base with a slight odor and is reactive to active metals such as sodium, potassium, magnesium and zinc.

MOCA is used to make polyurethane products that are a significant component of many common appliances.
These are widely used in such items as gear systems in modern office and home appliances, sporting goods, mouldings for motor vehicle body parts and military equipment.

MOCA is commonly used as a coating to set other glues, plastics and adhesives.
MOCA's main purpose is to act as a curing agent for other polyurethane and elastomer compounds.
MOCA is essential for creating chemical reactions that bond other molecules in relatively stable complex structures which comprise these compounds.

MOCA is a synthetic chemical used primarily to make polyurethane products.
Pure MOCA is a colorless, crystalline solid, but the commonly used form is usually yellow, tan, or brown pellets.

MOCA has no smell or taste.
Examples of these products include gears, gaskets, sport boots, roller skate wheels, shoe soles, rolls and belt drives in cameras, computers and copy machines, wheels and pulleys for escalators and elevators, components in home appliances, and various military applications.

MOCA is also used as a coating in chemical reactions to "set" glues, plastics, and adhesives.
Because plastics have many uses, MOCA is widely used.

Uses of MOCA:
MOCA is primarily used as a curing agent for cast polyurethane elastomers.
MOCA is commonly applied in industrial products such as rollers, wheels, seals, gaskets, and abrasion-resistant parts.
MOCA is also used in coatings, adhesives, and sealants where high strength and thermal stability are required.

MOCA is used as a curing agent for liquid polyurethane elastomers.
These elastomers have been used to produce shoe soles; rolls for postage stamp machines; cutting bars in plywood manufacturing; rolls and belt drives in cameras, computers, and reproducing equipment; and pulleys for escalators and elevators.
MOCA is widely used in machinery, automobile, aircraft manufacturing, mining, industrial and sports facilities (such as plastic track and plastic floor) can be used for curing and waterproof coatings such as epoxy resin, which can be given to polyester and polyether elastomer most good physical and mechanical properties and the results.

MOCA has been used principally as a curing agent for polyurethanes and epoxy resins, which are then used in the manufacture of specialized products, particularly integral-skin polyurethane semirigid foam (used for crash padding) and solid urethane rubber molding such as gear blanks and industrial tires.
MOCA has been added to vary the hardness, flexibility, and impact strength of these products.
More than 99% of MOCA has been reported as used to manufacture polyurethanes.

MOCA is used principally as a curing agent for polyurethane prepolymers in the manufacturing of high-performance, specialized, castable urethane rubber products.
Mouldings such as industrial tyres and rollers, shock absorption pads and conveyor belting are among the wide variety of uses.
A use of MOCA that is specific to Japan and the Far East is as a curing agent in roofing and wood sealing.

Industry Uses:
Catalyst
Process regulators
Intermediate
Plasticizers

Consumer Uses:
Plasticizers

Chemical Properties of MOCA:
MOCA is a synthetic chemical used to make polyurethane.
MOCA is moderately soluble in water but soluble in alcohol, ether, organic and some solvents.

MOCA can be gradually broken down by the action of sunlight in air and by microscopic organisms in soil or water.
When heated to the point of decomposing MOCA gives off toxic fumes of hydrochloric acid, complex organic compounds and oxides of nitrogen.

Production Methods of MOCA:
The production of MOCA in the United States has ceased since 1979 and is now imported, mainly from Japan.
More than 1.9 million lb was imported in 1989.

MOCA is currently used as a curing agent for isocyanate-containing polymers and in the manufacture of polyurethane foams, epoxy resins, gun mounts, jet engine turbine blades, radar systems, and components in home appliances.
MOCA is also a model compound for studying carcinogenesis.

Stability and Reactivity of MOCA:

Chemical stability:
Stable under normal conditions.

Reactivity:
Reacts with isocyanates to form polyurethane networks.

Conditions to avoid:
Excessive heat.
Strong oxidizing agents.

Incompatible materials:
Strong oxidizers.
Strong acids.

Hazardous decomposition products:
Toxic fumes including hydrogen chloride (HCl) may form under fire conditions.
Nitrogen oxides (NOₓ) may form under fire conditions.

Handling and Storage of MOCA:

Handling:
Use proper personal protective equipment (PPE).
Avoid dust formation.
Avoid contact.

Storage:
Store in a cool, dry, well-ventilated area.

Storage conditions:
Keep container tightly closed.

First Aid Measures of MOCA:

Inhalation:
Move to fresh air immediately.

Skin contact:
Wash with soap and water.

Eye contact:
Rinse with water for at least 15 minutes.

Ingestion:
Seek immediate medical attention.

Firefighting Measures of MOCA:

Extinguishing media:
Foam.
Dry chemical.
Carbon dioxide (CO₂).

Hazards:
Toxic gases may form.
Hydrogen chloride (HCl).
Nitrogen oxides (NOₓ).

Protection:
Use full protective equipment.
Use self-contained breathing apparatus.

Accidental Release Measures of MOCA:

Personal precautions:
Wear protective equipment.

Environmental precautions:
Prevent release into the environment.

Cleanup:
Collect solid material carefully.
Dispose properly.

Exposure Controls / Personal Protection of MOCA:

Respiratory protection:
Use appropriate mask if dust forms.

Hand protection:
Chemical-resistant gloves.

Eye protection:
Safety goggles.

Skin protection:
Protective clothing.

Identifiers of MOCA:
CAS Number: 101-14-4
EC Number: 202-918-9
Molecular Formula: C₁₃H₁₂Cl₂N₂
Molecular Weight: ~267.15 g/mol

CAS No.: 101-14-4
Chemical Name: 4,4'-Methylene bis(2-chloroaniline)
CBNumber: CB1495681
Molecular Formula: C13H12Cl2N2
Molecular Weight: 267.15
MDL Number: MFCD00047829

Product Number: M0609
Purity / Analysis Method : >85.0%(HPLC)
Molecular Formula / Molecular Weight: C13H12Cl2N2 = 267.15 
Physical State (20 deg.C): Solid
Storage Temperature : Room Temperature (Recommended in a cool and dark place, <15°C)
CAS RN: 101-14-4
Reaxys Registry Number: 1882318
PubChem Substance ID: 87572634
SDBS (AIST Spectral DB): 7183
Merck Index (14): 6059
MDL Number: 
MFCD00047829

CAS Number: 101-14-4
ChEMBL: ChEMBL82846
ChemSpider: 7262
ECHA InfoCard: 100.002.654
KEGG: C10999
PubChem CID: 7543
UNII: 3L2W5VTT2A
CompTox Dashboard (EPA): DTXSID5020865
InChI: InChI=1S/C13H12Cl2N2/c14-10-6-8(1-3-12(10)16)5-9-2-4-13(17)11(15)7-9/h1-4,6-7H,5,16-17H2
Key: IBOFVQJTBBUKMU-UHFFFAOYSA-N
InChI=1/C13H12Cl2N2/c14-10-6-8(1-3-12(10)16)5-9-2-4-13(17)11(15)7-9/h1-4,6-7H,5,16-17H2
Key: IBOFVQJTBBUKMU-UHFFFAOYAI
SMILES: Clc1cc(ccc1N)Cc2ccc(N)c(Cl)c2

Linear Formula: CH2[C6H3(Cl)NH2]2
CAS Number: 101-14-4
Molecular Weight: 267.15
UNSPSC Code: 12162002
NACRES: NA.23
PubChem Substance ID: 24847326
EC Number: 202-918-9
Beilstein/REAXYS Number: 1882318
MDL number: MFCD00047829

Properties of MOCA:
Appearance: Light yellow to tan solid
Odor: Slight amine odor
Density: ~1.26 g/cm³
Melting Point: ~100–110°C
Solubility: Low in water, soluble in organic solvents
Reactivity: Reacts with isocyanates

Chemical formula: C13H12Cl2N2
Molar mass: 267.15 g·mol−1
Appearance: Tan-colored pellets or flakes
Odor: faint, amine-like
Density: 1.44 g/cm3
Melting point: 104 to 109 °C (219 to 228 °F; 377 to 382 K)
Solubility in water: insoluble
Vapor pressure: 0.00001 mmHg (20 °C)

Melting Point: 108 °C
Solubility in water: Insoluble
Solubility (soluble in): Toluene, Ethanol, Benzene

Quality Level: 100
assay: 85%
form: solid
bp: 202-214 °C/0.3 mmHg (lit.)
mp: 102-107 °C (lit.)
SMILES string: Nc1ccc(Cc2ccc(N)c(Cl)c2)cc1Cl
InChI: 1S/C13H12Cl2N2/c14-10-6-8(1-3-12(10)16)5-9-2-4-13(17)11(15)7-9/h1-4,6-7H,5,16-17H2
InChI key: IBOFVQJTBBUKMU-UHFFFAOYSA-N

Melting point: 102-107 °C(lit.)
Boiling point: 202-214 °C0.3 mm Hg(lit.)
Density: 1.44
vapor pressure: 0.001Pa at 20℃
refractive index: 1.6710 (estimate)
Flash point: >230 °F
solubility: Acetonitrile (Slightly), DMSO (Slightly), Methanol (Slightly)
pka: 3.33±0.25(Predicted)
form: solid
color: Light orange to Yellow to Green
Water Solubility: <0.1 g/100 mL at 25 ºC
Merck: 14,6059
BRN: 1882318
Henry's Law Constant: 9.0×105 mol/(m3Pa) at 25℃, HSDB (2015)
Stability: Stable, but decomposes exothermically, and possibly explosively, above 200 C. Incompatible with strong oxidizing agents.
Major Application: environmental
InChI: 1S/C13H12Cl2N2/c14-10-6-8(1-3-12(10)16)5-9-2-4-13(17)11(15)7-9/h1-4,6-7H,5,16-17H2
InChIKey: IBOFVQJTBBUKMU-UHFFFAOYSA-N
SMILES: Nc1ccc(Cc2ccc(N)c(Cl)c2)cc1Cl

Molecular Weight: 267.15 g/mol
XLogP3: 3.8
Hydrogen Bond Donor Count: 2
Hydrogen Bond Acceptor Count: 2
Rotatable Bond Count: 2
Exact Mass: 266.0377538 Da
Monoisotopic Mass: 266.0377538 Da
Topological Polar Surface Area: 52 Ų
Heavy Atom Count: 17
Complexity: 226
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes

Specifications of MOCA:
Appearance: Light orange to Yellow to Green powder to crystal
Purity(HPLC): min. 85.0 area%
Purity(Nonaqueous Titration): min. 98.0 %
Melting point: 104.0 to 109.0 °C

Names of MOCA:

Preferred IUPAC name:
4,4′-Methylenebis(2-chloroaniline)

Other names:
4,4′-Methylene-bis(2-chloroaniline)
Cyanaset
Quodorole
Dacpm
Curalin M
Diamet Kh
Millionate M
Bis amine
MOCA
Bisamine S