CAS 2892-62-8 Dibutyl squarate (HCID 65108)

Overview

Squaric acid dibutyl ester is a cyclic ketone and diether that is a dibutyl ether derivative of squaric acid. It has a role as an immunological adjuvant and an allergen. It is a cyclic ketone and a diether. It is functionally related to a squaric acid.

Names & identifiers

Preferred name: Dibutyl squarate
IUPAC: 3,4-dibutoxycyclobut-3-ene-1,2-dione
English name: Dibutyl squarate
Molecular formula: C12H18O4
Molecular weight: 226.27

Names & synonyms

2892-62-8Dibutyl squarate3,4-dibutoxycyclobut-3-ene-1,2-dione3,4-Dibutoxy-3-cyclobutene-1,2-dioneSquaric acid dibutyl esterSADBESquaric acid dibutylester4RTO57VG65SQX770NSC-113489CHEBI:53612SQX-770

Show more names

di-n-butyl squarateTIMTEC-BB SBB007902SQUARIC ACID DI-N-BUTYL ESTERSquaric acid dibutyl ester,97%Di-n-butyl squarate~Squaric ac

DTXSID30183113RefChem:185167DTXCID40105604628-906-73-Cyclobutene-1,2-dione, 3,4-dibutoxy-3,4-di-n-Butoxy-3-cyclobutene-1,2-dioneMFCD000371501,2-dibutyl squarate

Database identifiers

CAS: 2892-62-8
PubChem CID: 65108
DTXSID: DTXSID30183113
ChEMBL: CHEMBL2435707
ChEBI: CHEBI:53612
UNII: 4RTO57VG65
EC Number: 628-906-7
Nikkaji: J382.983I

Properties

Computed structural properties

XLogP: 2.4
Topological polar surface area: 52.6 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 4
Rotatable bonds: 8
Heavy atoms: 16
Formal charge: 0
Complexity: 274

Experimental & physicochemical properties

DrugsPharmaceuticals -> Listed in ZINC15

Physicochemical properties

Boiling point: 139 °C0.5 · 139 °C0.5 mm Hg(lit.)
Density: 1.047 g/mL · 1.047 g/mL at 25 °C(lit.)
refractive index: 20 · n20/D 1.494(lit.)
Flash point: 230 °F · >230 °F
storage temp.: Sealed in dry,Room Temperature
form: Liquid
color: Clear colorless to yellow
Water Solubility: INSOLUBLE
BRN: 1968189 · 1968189
InChI: InChI=1S/C12H18O4/c1-3-5-7-15-11-9(13)10(14)12(11)16-8-6-4-2/h3-8H2,1-2H3
InChIKey: XBRWELTXMQSEIN-UHFFFAOYSA-N
SMILES: C1(=O)C(OCCCC)=C(OCCCC)C1=O
CAS DataBase Reference: 2892 · 2892-62-8(CAS DataBase Reference)
FDA UNII: 4 RTO57VG65 · 4RTO57VG65
NIST Chemistry Reference: Dibutyl squarate(2892-62-8)
UNSPSC Code: 12352100 · 12352100
NACRES: 22 · NA.22
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 315 · H315-H317-H319-H335
Precautionary statements: 280 · P280-P302+P352-P305+P351+P338
target organs: Respiratory system
PPE: Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
Hazard Codes: Xn
Risk Statements: 36 · 36/37/38-42/43
Safety Statements: 26 · 26-27-36/37/39-45
WGK Germany: 3 · 3
RTECS: 1772066 · GU1772066
HS Code: 29145090 · 29145090
Storage Class: 10 · 10 - Combustible liquids
Hazard Classifications: 2 Skin · Eye Irrit. 2Skin Irrit. 2Skin Sens. 1STOT SE 3

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H315 (100%): 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 46 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Hazard Classes and CategoriesSkin Irrit. 2 (100%)

Safety data

PPE: Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
wgk: 3
rtecs: GU1772066
hs_code: 29145090
risk_code: 36/37/38-42/43
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xn
safety_code: 26-27-36/37/39-45
Storage Class: 10 - Combustible liquids
target organs: Respiratory system
Hazard statements: H315-H317-H319-H335
Hazard Classifications: Eye Irrit. 2Skin Irrit. 2Skin Sens. 1STOT SE 3
Precautionary statements: P280-P302+P352-P305+P351+P338

Chemistry & industry

Pharmacology

MeSH Pharmacological Classification · 1 item

Substances that augment, stimulate, activate, potentiate, or modulate the immune response at either the cellular or humoral level. The classical agents (Freund's adjuvant, BCG, Corynebacterium parvum, et al.) contain bacterial antigens. Some are endogenous (e.g., histamine, interferon, transfer factor, tuftsin, interleukin-1). Their mode of action is either non-specific, resulting in increased immune responsiveness to a wide variety of antigens, or antigen-specific, i.e., affecting a restricted type of immune response to a narrow group of antigens. The therapeutic efficacy of many biological response modifiers is related to their antigen-specific immunoadjuvanticity.

Applications · 3 items

Uses3,4-Dibutoxy-3-cyclobutene-1,2-dione was used in the synthesis of novel semisquarylium dye, useful for highly selective Hg2+ sensing in aqueous media. It was also employed in the synthesis of 3-butoxy-4-(1,3,3-trimethyl-2,3-dihydro-1H-2-indolylidenemethyl)-3-cyclobutene-1,2-dione, intermediate for the synthesis of squaryl dyes.

UsesSquaric acid and its derivatives (Dibutyl squarate) are used in synthesis of pharmaceutical intermediates, squarylium dyes, and photoconducting squaraines.

General Description3,4-Dibutoxy-3-cyclobutene-1,2-dione is the dialkyl ester of squaric acid.