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4,4'-Methylenebis(2-chloroaniline)

4,4′-Methylenebis(2-chloroaniline) (also known as MOCA, MBOCA, and bisamine) is a substance used as a curing agent in polyurethane production.[3] 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. It 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.[1]

4,4′-Methylenebis(2-chloroaniline)
Names
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
Identifiers
  • 101-14-4 Y
3D model (JSmol)
  • Interactive image
ChEMBL
  • ChEMBL82846 Y
ChemSpider
  • 7262 Y
ECHA InfoCard 100.002.654
KEGG
  • C10999 Y
  • 7543
UNII
  • 3L2W5VTT2A N
  • DTXSID5020865
  • 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 Y
    Key: IBOFVQJTBBUKMU-UHFFFAOYSA-N Y
  • 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
  • Clc1cc(ccc1N)Cc2ccc(N)c(Cl)c2
Properties
C13H12Cl2N2
Molar mass 267.15 g·mol−1
Appearance Tan-colored pellets or flakes[1]
Odor faint, amine-like[1]
Density 1.44 g/cm3[1]
Melting point 104 to 109 °C (219 to 228 °F; 377 to 382 K)[2]
insoluble
Vapor pressure 0.00001 mmHg (20 °C)[1]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
potential occupational carcinogen[1]
NFPA 704 (fire diamond)
Health 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
1
0
Flash point 203 °C (397 °F; 476 K)
NIOSH (US health exposure limits):
PEL (Permissible)
none[1]
REL (Recommended)
Ca TWA 0.003 mg/m3 [skin][1]
IDLH (Immediate danger)
Ca [N.D.][1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)

It is a weak base with a slight odor and is reactive to active metals such as sodium, potassium, magnesium and zinc.[1]

Toxicity edit

Employee exposure is often monitored by measurement of urinary MOCA in free and/or conjugated form.[4] The best currently available indicator of absorption of MOCA is urinary total MOCA estimations based on spot creatinine corrected urines. Although this method is not without limitations, that is unmetabolised MOCA is measured and dose-response curves are lacking, its use is a reasonable means of monitoring the effectiveness of engineering controls, personal protective equipment and work practices including education. MOCA levels are usually higher at the end of the shift and reflect exposure over the preceding two to three days. The biological half-life of MOCA in urine is approximately 23 hours.

Regulation edit

In December, 2023, the US EPA announced that it was prioritizing MBOCA "for risk evaluation under the Toxic Substances Control Act (TSCA)" along with four other toxic chemicals.[5]

References edit

  1. ^ a b c d e f g h i j NIOSH Pocket Guide to Chemical Hazards. "#0411". National Institute for Occupational Safety and Health (NIOSH).
  2. ^ "4,4'-Methylenebis(2-chloroaniline)". TCI Chemicals. Retrieved March 17, 2014.
  3. ^ RTK HSFS 1250
  4. ^ , Occupational Safety and Health Administration
  5. ^ "EPA Begins Process to Prioritize Five Chemicals for Risk Evaluation Under Toxic Substances Control Act". US EPA. December 14, 2023. Retrieved 8 February 2024.

methylenebis, chloroaniline, methylenebis, chloroaniline, also, known, moca, mboca, bisamine, substance, used, curing, agent, polyurethane, production, moca, aromatic, amine, which, structurally, similar, benzidine, known, human, bladder, carcinogen, moca, bee. 4 4 Methylenebis 2 chloroaniline also known as MOCA MBOCA and bisamine is a substance used as a curing agent in polyurethane production 3 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 It 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 1 4 4 Methylenebis 2 chloroaniline NamesPreferred IUPAC name 4 4 Methylenebis 2 chloroaniline Other names 4 4 Methylene bis 2 chloroaniline CyanasetQuodoroleDacpmCuralin MDiamet KhMillionate MBis amineMOCABisamine SIdentifiersCAS Number 101 14 4 Y3D model JSmol Interactive imageChEMBL ChEMBL82846 YChemSpider 7262 YECHA InfoCard 100 002 654KEGG C10999 YPubChem CID 7543UNII 3L2W5VTT2A NCompTox Dashboard EPA DTXSID5020865InChI 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 YKey IBOFVQJTBBUKMU UHFFFAOYSA N YInChI 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 17H2Key IBOFVQJTBBUKMU UHFFFAOYAISMILES Clc1cc ccc1N Cc2ccc N c Cl c2PropertiesChemical formula C 13H 12Cl 2N 2Molar mass 267 15 g mol 1Appearance Tan colored pellets or flakes 1 Odor faint amine like 1 Density 1 44 g cm3 1 Melting point 104 to 109 C 219 to 228 F 377 to 382 K 2 Solubility in water insolubleVapor pressure 0 00001 mmHg 20 C 1 HazardsOccupational safety and health OHS OSH Main hazards potential occupational carcinogen 1 NFPA 704 fire diamond 210Flash point 203 C 397 F 476 K NIOSH US health exposure limits PEL Permissible none 1 REL Recommended Ca TWA 0 003 mg m3 skin 1 IDLH Immediate danger Ca N D 1 Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references It is a weak base with a slight odor and is reactive to active metals such as sodium potassium magnesium and zinc 1 Toxicity editEmployee exposure is often monitored by measurement of urinary MOCA in free and or conjugated form 4 The best currently available indicator of absorption of MOCA is urinary total MOCA estimations based on spot creatinine corrected urines Although this method is not without limitations that is unmetabolised MOCA is measured and dose response curves are lacking its use is a reasonable means of monitoring the effectiveness of engineering controls personal protective equipment and work practices including education MOCA levels are usually higher at the end of the shift and reflect exposure over the preceding two to three days The biological half life of MOCA in urine is approximately 23 hours Regulation editIn December 2023 the US EPA announced that it was prioritizing MBOCA for risk evaluation under the Toxic Substances Control Act TSCA along with four other toxic chemicals 5 References edit a b c d e f g h i j NIOSH Pocket Guide to Chemical Hazards 0411 National Institute for Occupational Safety and Health NIOSH 4 4 Methylenebis 2 chloroaniline TCI Chemicals Retrieved March 17 2014 RTK HSFS 1250 4 4 Methylene bis 2 chloroaniline Health Guideline Occupational Safety and Health Administration EPA Begins Process to Prioritize Five Chemicals for Risk Evaluation Under Toxic Substances Control Act US EPA December 14 2023 Retrieved 8 February 2024 Retrieved from https en wikipedia org w index php title 4 4 27 Methylenebis 2 chloroaniline amp oldid 1204964916, wikipedia, wiki, book, books, library,

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