Dithiodibenzoic acid (HCID 8409)

Names & identifiers

Preferred name: Dithiodibenzoic acid
IUPAC: 2-[(2-carboxyphenyl)disulfanyl]benzoic acid
English name: 2,2'-Dithiosalicylic acid
Molecular formula: C14H10O4S2
Molecular weight: 306.36

Names & synonyms

dithiodibenzoic acidRefChem:80733119-80-22,2'-Dithiodibenzoic acid2,2'-Dithiosalicylic acid2-[(2-Carboxyphenyl)disulfanyl]benzoic acidBenzoic acid, 2,2'-dithiobis-2,2'-disulfanediyldibenzoic acidBis(2-carboxyphenyl) disulfide2,2'-dithiobisbenzoic acidBenzoic acid, dithiobis-Bis(o-carboxylphenyl) disulfide

Show more names

DSTADITHIOSALICYLIC ACID2,2'-DITHIOBENZOIC ACIDDithioslicylicacidNSC 213NSC 405662NSC 633230

2,2'-Dithiodi(benzoic acid)2,2'-Dithiobis(benzoic acid)Diphenyldisulfide-2,2'-dicarboxylic acidNSC 5346MFCD00002465Diphenyl disulfide-2,2'-dicarboxylic acidNSC-405662BENZOIC ACID, 2,2'-DITHIODI-

Database identifiers

CAS: 119-80-2
PubChem CID: 8409
DTXSID: DTXSID1059498
ChEMBL: CHEMBL118378
UNII: 58MGB5279D
EC Number: 204-352-8
Nikkaji: J31.929E

Properties

Computed structural properties

XLogP: 3.1
Topological polar surface area: 125 Å²
Hydrogen bond donors: 2
Hydrogen bond acceptors: 6
Rotatable bonds: 5
Heavy atoms: 20
Formal charge: 0
Complexity: 327

Experimental & physicochemical properties

Chemical ClassesOther Classes -> Other Aromatic Compounds

SolubilitySolubility in water: none

Melting Point287 - 290 °C

Physical Description · 2 items

White to yellow solid; [ICSC] Yellow or brown powder; [Alfa Aesar MSDS]

WHITE-TO-YELLOW POWDER.

Physicochemical properties

Melting point: 287 · 287-290 °C(lit.)
Boiling point: 416.97 °C · 416.97°C (rough estimate)
Density: 1.4555 · 1.4555 (rough estimate)
vapor pressure: 0 Pa · 0Pa at 25℃
refractive index: 1.495 · 1.4950 (estimate)
storage temp.: Refrigerator
solubility: DMSO (Slightly), Methanol (Slightly)
pka: 3.02 · 3.02±0.36(Predicted)
form: Powder
color: Brown
Water Solubility: insoluble
BRN: 2221810 · 2221810
InChI: 1S/C14H10O4S2/c15-13(16)9-5-1-3-7-11(9)19-20-12-8-4-2-6-10(12)14(17)18/h1-8H,(H,15,16)(H,17,18)
InChIKey: LBEMXJWGHIEXRA-UHFFFAOYSA-N
SMILES: OC(=O)c1ccccc1SSc2ccccc2C(O)=O
LogP: 1.61 at · 1.61 at 25℃ and pH6.2-6.48
CAS DataBase Reference: 119 · 119-80-2(CAS DataBase Reference)
FDA UNII: 58 MGB5279D · 58MGB5279D
EPA Substance Registry System: 2 · Benzoic acid, 2,2'-dithiobis- (119-80-2)
UNSPSC Code: 41116107 · 41116107
NACRES: 24 · NA.24
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 315 · H315-H319-H335
Precautionary statements: 261 · P261-P280a-P304+P340-P305+P351+P338-P405-P501a-P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313
PPE: 95 · dust mask type N95 (US), Eyeshields, Gloves
Hazard Codes: Xi
Risk Statements: 36 · 36/37/38
Safety Statements: 26 · 26-36-24/25
WGK Germany: 3 · 3
RTECS: 9660000 · DG9660000
Hazard Note: Harmful/irritant
TSCA: TSCA listed
HS Code: 29309070 · 29309070
Storage Class: 11 · 11 - Combustible Solids
Toxicity: 50 ipr-mus: · LD50 ipr-mus: 367 mg/kg ARZNAD 21,284,71
REACH Registrations: Active

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H315 (99.9%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P272, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P333+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 2063 reports by companies from 14 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information · 2 items

Status: Active Update: 25-03-2013 https://echa.europa.eu/registration-dossier/-/registered-dossier/11157

Benzoic acid, 2,2'-dithiobis-: Does not have an individual approval but may be used under an appropriate group standard

Fire HazardsCombustible. Gives off irritating or toxic fumes (or gases) in a fire.

Hazards SummaryUse protective gloves and glasses when handling; No listed effects of short-term or long-term exposure; Produces corrosive fumes if burned; [ICSC] An irritant; [Alfa Aesar MSDS]

Chemical DangersDecomposes on burning. This produces corrosive fumes including sulfur oxides.

Hazard Classes and CategoriesSkin Irrit. 2 (99.9%)

Safety & protection

Fire FightingUse water spray, foam, powder, carbon dioxide.

First Aid Measures · 3 items

Rinse skin with plenty of water or shower.

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth. Give one or two glasses of water to drink. Refer for medical attention .

Safe StorageSeparated from strong oxidants. Store in an area without drain or sewer access.

Spillage Disposal · 1 item

Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Do NOT let this chemical enter the environment.

Eye PreventionWear safety spectacles.

Fire PreventionNO open flames.

Toxicology

Signs and Symptoms · 3 items

Cough.

Redness.

ICSC Environmental DataEnvironmental effects from the substance have not been investigated adequately.

Safety data

PPE: dust mask type N95 (US), Eyeshields, Gloves
wgk: 3
tsca: TSCA listed
rtecs: DG9660000
hs_code: 29309070
Toxicity: LD50 ipr-mus: 367 mg/kg ARZNAD 21,284,71
risk_code: 36/37/38
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xi
hazard_note: Harmful/irritant
safety_code: 26-36-24/25
Storage Class: 11 - Combustible Solids
Hazard statements: H315-H319-H335
REACH Registrations: Active
Precautionary statements: P261-P280a-P304+P340-P305+P351+P338-P405-P501a-P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313

Chemistry & industry

Uses & manufacturing

General Manufacturing InformationBenzoic acid, 2,2'-dithiobis-: ACTIVE

Applications · 3 items

Uses2,2'-Dithiosalicylic acid is an organosulfur compound produced from dibenzothiophene metabolites that is in turn biodegraded into transient metabolites such as benzoic acid.It is used in the preparation of a new class of anti-HIV-1 agents.

Uses2,2′-Dithiodibenzoic acid may be used for the preparation of novel anionic heptadecanuclear silver(I) cluster, by the reaction with equivalent molar silver oxide under ultrasonic conditions at 50°C. It may be used for the preparation of polyamides containing a disulfide bond in their main chain.

General Description2,2′-Dithiodibenzoic acid is an sulfhydryl modifying reagent. 2,2′-Dithiodibenzoic acid on cocrystallization with imidazole or 4-methylimidazole affords bis(imidazolium) 2,2′-dithiodibenzoate and 4-methylimidazolium 2-[(2-carboxyphenyl)disulfanyl]benzoate organic salt, respectively. It also cocrystallizes with isonicotinohydrazide from methanol solution to afford the 1:2 cocrystal, 2,2′-dithiodibenzoic acid-isonicotinohydrazide.