Basic information
- Standard SMILES
Cc1cc(O)c(C(C)(C)C)cc1Sc1cc(C(C)(C)C)c(O)cc1C- InChIKey
HXIQYSLFEXIOAV-UHFFFAOYSA-N- Molecular formula
- C22H30O2S
- Average molar mass
- 358.5 g/mol
- Monoisotopic mass
- 358.1966512
Overview
4,4'-thiobis(6-tert-butyl-m-cresol) appears as white or light gray to tan powder. (NTP, 1992)
Names & identifiers
- Preferred name
- Santonox
- IUPAC
- 2-tert-butyl-4-(5-tert-butyl-4-hydroxy-2-methylphenyl)sulfanyl-5-methylphenol
- English name
- 4,4'-Thiobis(6-tert-butyl-m-cresol)
- Molecular formula
- C22H30O2S
- Molecular weight
- 358.54
Names & synonyms
Show more names
Database identifiers
- CAS
57062-46-1、96-69-5- PubChem CID
- 7308
- DTXSID
DTXSID4021341- ChEMBL
CHEMBL1526319- UNII
- 3CA5G9822V
- EC Number
- 202-525-2
- Nikkaji
- J5.161F
Properties
Computed structural properties
- XLogP
- 7.4
- Topological polar surface area
- 65.8 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 4
- Heavy atoms
- 25
- Formal charge
- 0
- Complexity
- 396
Experimental & physicochemical properties
Polymers
Plastics & Rubber -> Curing Agents (Aromatic)
Plastics -> Antioxidants
Plastics -> Polyolefin-I
Density
1.1 at 77 °F (NTP, 1992) - Denser than water; will sink
1.10
1.10 @25 °C
1.10
Color/Form
LIGHT GREY POWDER
FINE WHITE CRYSTALS
Light gray to tan powder.
Solubility
less than 0.1 mg/mL at 64 °F (NTP, 1992)
VERY SOL IN METHANOL (79%); SOL IN ACETONE (20%); SLIGHTLY SOL IN BENZENE (5%); VERY SLIGHTLY SOL IN WATER (0.08%)
0.08%
Flash Point
420 °F (NTP, 1992)
420 °F
420 °F
420 °F
Melting Point
302 °F (NTP, 1992)
150 °C
SANTONOX R MELTING POINT: 161 °C
302 °F
150 °C
302 °F
Vapor Pressure
6.3e-07 mmHg at 158 °F (NTP, 1992)
0.0000006 mmHg
0.0000006 mmHg
Physical Description
4,4'-thiobis(6-tert-butyl-m-cresol) appears as white or light gray to tan powder. (NTP, 1992)
Dry Powder
Light-gray to tan powder with a slightly aromatic odor; [NIOSH]
Light-gray to tan powder with a slightly aromatic odor.
Light-gray to tan powder with a slightly aromatic odor.
Physicochemical properties
- Melting point
- 160 · 160-165 °C
- Boiling point
- 460.94 °C · 460.94°C (rough estimate)
- Density
- 1.06 · 1.06~1.12g/cm3
- vapor pressure
- 0.001 Pa · 0.001Pa at 20℃
- refractive index
- 1.52 · 1.5200 (estimate)
- Flash point
- 215 °C · 215 °C
- storage temp.
- 30 °C · Store below +30°C.
- solubility
- DMSO (Slightly), Methanol (Slightly)
- pka
- 10.76 · 10.76±0.36(Predicted)
- form
- Fine white to gray powder.
- color
- White to Off-White
- Water Solubility
- 0.01 g/100 · <0.01 g/100 mL at 18 ºC
- Stability
- Stable under recommended storage conditions., Stable Under Recommended Storage C
- InChI
- 1S/C22H30O2S/c1-13-9-17(23)15(21(3,4)5)11-19(13)25-20-12-16(22(6,7)8)18(24)10-14(20)2/h9-12,23-24H,1-8H3
- InChIKey
- HXIQYSLFEXIOAV-UHFFFAOYSA-N
- SMILES
- Cc1cc(O)c(cc1Sc2cc(c(O)cc2C)C(C)(C)C)C(C)(C)C
- LogP
- 5.24 at · 5.24 at 25℃
- Toxicology and Carcinogenesis
- 4 · Toxicology and Carcinogenesis Studies of 4,4'-Thiobis(6-t-butyl-m-cresol) (CASRN 96-69-5) in F344/N Rats and B6C3F1 Mice (Feed Studies)
- FDA 21 CFR
- 175.105 · 175.105; 177.2600; 178.2010
- Indirect Additives used in Food Contact Substances
- 4 · 4,4'-THIOBIS(6-TERT-BUTYL-M-CRESOL)
- CAS DataBase Reference
- 96 · 96-69-5(CAS DataBase Reference)
- FDA UNII
- 3 CA5G9822V · 3CA5G9822V
- NIST Chemistry Reference
- 4 · 4,4'-Thiobis(3-methyl-6-t-butylphenol)(96-69-5)
- EPA Substance Registry System
- 4 · 4,4'-Thiobis(6-tert-butyl-m-cresol) (96-69-5)
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 7 · GHS07,GHS09
- Signal word
- Warning
- Hazard statements
- 317 · H317-H410
- Precautionary statements
- 261 · P261-P272-P273-P280-P302+P352-P333+P313
- Hazard Codes
- Xi,N
- Risk Statements
- 36 · 36/37/38-50/53-43
- Safety Statements
- 37 · 37/39-26-61-60-36/37-24/25
- RIDADR
- 3077 · UN3077
- OEB
- B
- OEL
- 10 mg/m3 · TWA: 10 mg/m3 (total)
- WGK Germany
- 2 water · WGK 2 water endangering
- RTECS
- 3150000 · GP3150000
- Autoignition Temperature
- 402 °C · 402 °C
- TSCA
- TSCA listed
- HazardClass
- 9 · 9
- HS Code
- 29309070 · 29309070
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 1 Aquatic · Aquatic Acute 1Aquatic Chronic 1Skin Sens. 1
- Hazardous Substances Data
- 96 · 96-69-5(Hazardous Substances Data)
- Toxicity
- 50 orally · LD50 orally in Rabbit: 2345 mg/kg
- REACH Registrations
- Active
- Limited Quantities
- 5 kg · 5.0 kg (11 lbs) (solid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 0.2% (2 of 807) of reports.
Warning
H317 (96.5%): May cause an allergic skin reaction [Warning Sensitization, Skin]
P261, P264+P265, P272, P273, P280, P302+P352, P305+P351+P338, P321, P333+P317, P337+P317, P362+P364, P391, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 807 reports by companies from 23 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Warning
Hazard information
Regulatory Information
Chemical: Phenol, 4,4'-thiobis[2-(1,1-dimethylethyl)-5-methyl-
Phenol, 4,4'-thiobis[2-(1,1-dimethylethyl)-5-methyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Phenol, 4,4'-thiobis[2-(1,1-dimethylethyl)-5-methyl- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)
Status: Active Update: 24-09-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/16037
Phenol, 4,4'-thiobis[2-(1,1-dimethylethyl)-5-methyl-: Does not have an individual approval but may be used under an appropriate group standard
Hazards Summary
Liver toxicity observed in 2-year feeding studies of rodents; Two patients had positive patch tests after developing contact dermatitis from latex gloves containing Santonox, but this was not confirmed in three other studies that found no evidence of skin sensitization; TLV Basis is respiratory tract irritation; [ACGIH] A skin, eye, and respiratory tract irritant; [CAMEO]
Special Reports
Toxicology & Carcinogenesis Studies of 4,4'-Thiobis(6-t-butyl-m-cresol) in F344/N Rats and B6C3F1 Mice (Feed Studies). Technical Report Series No. 435 (1994) NTIS Publication No. 95-225751 U.S. Department of Health and Human Services, National Toxicology Program, National Institute of Environmental Health Sciences, Research Triangle Park, NC 27709
NIOSH Recommendations
Recommended Exposure Limit: 10 Hr Time-Weighted Avg: 10 mg/cu m (total).
Recommended Exposure Limit: 10 Hr Time-Weighted Avg: 5 mg/cu m (resp).
Hazard Classes and Categories
Skin Sens. 1 (96.5%)
Specific target organ toxicity - Repeated exposure - Category 2 (liver)
Acute toxicity (Oral) - Category 5
Safety & protection
First Aid
EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.
(General first aid procedures)
Nonfire Spill Response
SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with 60-70% ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with 60-70% ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.
Threshold Limit Values (TLV)
1.0 [mg/m3], Inhalable particulate matter
8 hr Time Weighted Avg (TWA): 10 mg/cu m. /4,4-Thiobis(6-tert-butyl-m-cresol)/
Excursion Limit Recommendation: Excursions in worker exposure levels may exceed three times the TLV-TWA for no more than a total of 30 min during a work day, and under no circumstances should they exceed five times the TLV-TWA, provided that the TLV-TWA is not exceeded. /4,4-Thiobis(6-tert-butyl-m-cresol)/
A4; Not classifiable as a human carcinogen. /4,4-Thiobis(6-tert-butyl-m-cresol)/
2008 Notice of Intended Changes: These substances, with their corresponding values and notations, comprise those for which (1) a limit is proposed for the first time, (2) a change in the Adopted value is proposed, (3) retention as an NIC is proposed, or (4) withdrawal of the Documentation and adopted TLV is proposed. In each case, the proposals should be considered trial values during the period they are on the NIC. These proposals were ratified by the ACGIH Board of Directors and will remain on the NIC for approximately one year following this ratification. If the Committee neither finds nor receives any substantive data that changes its scientific opinion regarding an NIC TLV, the Committee may then approve its recommendation to the ACGIH Board of Directors for adoption. If the Committee finds or receives substantive data that change its scientific opinion regarding an NIC TLV, the Committee may change its recommendation to the ACGIH Board of Directors for the matter to be either retained on or withdrawn from the NIC. Substance: 4,4-Thiobis(6-tert-butyl-m-cresol); Time Weighted Avg (TWA): 10.0 mg/cu m; Short Term Exposure Limit (STEL): None; Notations: A4; Not classifiable as a human carcinogen; Molecular Weight: 358.54; TLV Basis: Liver damage, upper and lower respiratory irritation.
1 mg/m³ (inhalable particulate matter) [2010]
Permissible Exposure Limit (PEL)
15.0 [mg/m3](total dust), 5 mg/m3(respirable fraction)
15 mg/m³ (total dust), 5 mg/m³ (respirable fraction)
TWA 15 mg/m3 (total) TWA 5 mg/m3 (resp) See Appendix G
Protective Action Criteria (PAC)
20 [mg/m3]
77 [mg/m3]
460 [mg/m3]
Recommended Exposure Limit (REL)
10 mg/m³ (total), 5 mg/m³ (resp)
TWA 10 mg/m3 (total) TWA 5 mg/m3 (resp)
Toxicology
Ongoing Test Status
The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical. [http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=96-69-5]
Carcinogen Classification
4,4-Thiobis(6-Tert-Butyl-m-Cresol)
TR-435: Toxicology and Carcinogenesis Studies of 4,4'-Thiobis(6-t-butyl-m-cresol) (CASRN 96-69-5) in F344/N Rats and B6C3F1 Mice (Feed Studies) (1994 )
06/22/93
No Evidence
No Evidence
No Evidence
Non-Human Toxicity Excerpts
THE LETHAL ORAL DOSE FOUND FOR RATS IS OF THE ORDER OF 5 G/KG BODY WEIGHT; BEFORE DEATH THE ANIMALS SHOWED SIGNS OF GASTROENTERITIS (SEVERE DIARRHEA).
RATS INGESTING DIETS CONTAINING 0.05% & 0.25% FOR 30 DAYS SHOWED NORMAL WT GAIN @ 0.05% LEVEL...BUT RETARDED WT GAIN & ENLARGED LIVERS @ 5-FOLD THIS LEVEL. /IN 90 DAY STUDIES NO TOXICITY/...RESULTED @ 0.005% LEVEL...BUT MALE RATS ON 0.05% DIET ATE & GREW SLIGHTLY LESS...NO PATHOLOGIC CHANGES WERE OBSERVABLE.
SANTONOX (80 MG/KG/DAY) GIVEN ORALLY FOR 10 DAYS TO RATS BEGINNING ON 5TH DAY AFTER TRANSPLANTATION OF YOSHIDA SARCOMA ENHANCED TUMOR DEVELOPMENT. THIS EFFECT MAY BE OWING TO DIRECT INFLUENCE ON REDOX PROCESSES WITHIN TUMOR CELLS OR OF LOWERED RESISTANCE OF ORGANISM.
4,4'-Thiobis(6-tert-butyl-m-cresol) was tested for mutagenicity in Salmonella/microsome preincubation assay using a protocol approved by the National Toxicology Program. A wide range of doses (0, 33, 100, 333, 1000, 3333, and 10,000 ug/plate) was tested in four Salmonella typhimurium strains (TA98, TA100, TA1535, and TA1537) in the presence and absence of Aroclor-induced rat or hamster liver S9. These tests were negative and the highest ineffective dose level tested (not causing the formation of a precipitate) in any Salmonella tester strain was 100 ug/plate.
... CONCLUSIONS: Under the conditions of these 2-year feed studies, there was no evidence of carcinogenic activity of TBBC in male or female F344/N rats administered 500, l,000, or 2,500 ppm or in male or female B6C3F1, mice administered 250, 500, or 1,000 ppm.
National Toxicology Program Studies
... Toxicology and carcinogenesis studies were conducted by administering 4,4'-thiobis(6-t-butyl-m-cresol) TBBC (99% pure) in feed to groups of male and female F344/N rats and B6C3F1 mice for ... 2 years. ... 2 YEAR STUDY IN RATS: ... Groups of 115 male and 75 female F344/N rats were fed diets containing 0, 500, 1,000, or 2,500 ppm TBBC for 2 years. Based on average daily feed consumption, these exposure levels resulted in a daily ingestion of TBBC of approximately 20, 40, or 100 mg/kg body weight for males and 20, 45, or 120 mg/kg body weight for females. 2 YEAR STUDY IN MICE: ... The doses selected for the 2 yr study were 250, 500, and 1,000 ppm. Groups of 80 male and 80 female mice were fed diets containing 0, 250, 500, or 1,000 ppm TBBC for 2 yr. Based on average daily feed consumption, these exposure levels resulted in the daily ingestion of approximately 30, 60, or 145 mg TBBC/kg body weight for males and 45, 110, or 255 mg TBBC/kg body weight for females. ... CONCLUSIONS: Under the conditions of these 2-year feed studies, there was no evidence of carcinogenic activity of TBBC in male or female F344/N rats administered 500, l,000, or 2,500 ppm or in male or female B6C3F1, mice administered 250, 500, or 1,000 ppm.
Safety data
- OEB
- B
- OEL
- TWA: 10 mg/m3 (total)
- wgk
- WGK 2 water endangering
- tsca
- TSCA listed
- rtecs
- GP3150000
- ridadr
- UN3077
- hs_code
- 29309070
- Toxicity
- LD50 orally in Rabbit: 2345 mg/kg
- risk_code
- 36/37/38-50/53-43
- Signal word
- Warning
- Symbol(GHS)
- GHS07,GHS09
- hazard_code
- Xi,N
- safety_code
- 37/39-26-61-60-36/37-24/25
- hazard_class
- 9
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H317-H410
- Limited Quantities
- 5.0 kg (11 lbs) (solid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
- REACH Registrations
- Active
- Hazard Classifications
- Aquatic Acute 1Aquatic Chronic 1Skin Sens. 1
- Autoignition Temperature
- 402 °C
- Precautionary statements
- P261-P272-P273-P280-P302+P352-P333+P313
- Hazardous Substances Data
- 96-69-5(Hazardous Substances Data)
Chemistry & industry
Uses & manufacturing
Uses
Used as an antioxidant in the manufacturing of synthetic rubber and plastics; [HSDB]
Plastic Composites Manufacturing [Category: Industry]
USED AS AN ANTIOXIDANT FOR POLYOLEFINES (HIGH- AND LOW-PRESSURE POLYETHYLENES, POLYPROPYLENE)
ANTIOXIDANT FOR SYNTHETIC RUBBERS & LATEXES
ANTIOXIDANT FOR NATURAL RUBBER & LATEX
STABILIZER FOR POLYETHYLENE, EG, FOOD PACKAGING FILMS
U.S. Exports
(1979) No Data
(1981) No Data
U.S. Imports
(1979) No Data
(1981) 6.50X10+7 GRAMS (PRINCPL CUSTMS DISTS)
U.S. Production
2023: 100,000 - <250,000 lb
(1979) PROBABLY GREATER THAN 4.54X10+5 GRAMS
(1981) PROBABLY GREATER THAN 4.54X10+5 GRAMS
Formulations/Preparations
SANTONOX CONTAINS A MAX OF 0.1% ASH AND 1% MOISTURE. SANTONOX R (RECRYSTALLIZED ANTIOXIDANT) CONTAINS MAX OF 0.05% ASH, 60 PPM & 0.2% CHLORIDES. /FROM TABLE/
THIS ANTIOXIDANT IS MADE BY MONSANTO CHEM CO, UNDER TRADE MARK SANTONOX. SANTONOX & SANTONOX R ARE TWO QUALITIES, THE SECOND BEING RECRYSTALLIZED ANTIOXIDANT.
Use Classification
Plastics -> Polymer Type -> Polyolefin-I
Plastics -> Antioxidants
General Manufacturing Information
Synthetic Rubber Manufacturing
Phenol, 4,4'-thiobis[2-(1,1-dimethylethyl)-5-methyl-: ACTIVE
.../THE COMPD IS/ AUTHORIZED FOR USE IN FOOD PACKAGINGS IN FRANCE AND ITALY. IN THE USA SANTONOX CONTENTS OF 0.05% OR LESS ARE AUTHORIZED FOR HIGH-PRESSURE POLYETHYLENE PACKAGINGS USED FOR FOODSTUFFS EXCLUDING FATS.
Applications
Description4,4'-Thiobis(6-tert-butyl-m-cresol) (Antioxidant 300), melting point 161-163℃, white powder, low volatility, low toxicity; soluble in organic solvents such as benzene, toluene, acetone, methanol, ethanol, carbon tetrachloride, slightly soluble in petroleum solvents, insoluble in water, is a non-polluting, high-efficiency phenolic antioxidant with low volatility, high antioxidant efficiency, good thermal stability and weather resistance, and little effect on the electrical properties of the product. It also has a synergistic effect when used with carbon black and octadecyl alcohol. It can be used as an antioxidant for polypropylene, ABS, polystyrene, polyphthalamide, polyurethane, etc., and is suitable for white, bright-colored and transparent products. It has very low toxicity and is allowed to be used in plastic products that come into contact with food in many countries.
Uses4,4''-Thiobis(2-tert-butyl-5-methylphenol) is an antioxidant in the rubber and plastics industry. 4,4''-Thiobis(2-tert-butyl-5-methylphenol) is a radical inhibitor which prevents the thermal decomposition of the peracid. In addition, it is used as a stabilizer in polyethylene and polyolefin packaging materials for foodstuffs. Protection of light-colored rubber from oxidation and of nonstaining neoprene compounds against deterioration.
General DescriptionWhite or light gray to tan powder.
Upstream & downstream products
Upstream raw materials
Suppliers50 total
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